A Day Between Three Tuscan Hilltops: What Nobody Tells You About Cortona, Montepulciano & Pienza

I'll be honest: the first time someone told me to visit three hill towns in one day, I thought it sounded exhausting. Steep streets, another church, another "best view in Tuscany" — how different could they really be?

Then I actually did it. And by the time I was sitting on a low stone wall in Pienza at golden hour, a piece of pecorino in one hand and absolutely no urge to be anywhere else, I understood why people build entire trips around this exact loop.

Here's what actually happened, town by town.

First Stop: Cortona, and the Staircase That Humbles Everyone

Nobody warns you about the Santa Margherita staircase. You see it from below, looking almost charming, and ten minutes later you're gripping a stone wall for support wondering if this is how Frances Mayes felt in Under the Tuscan Sun — except she had a house waiting at the top, and I just had a view.

And what a view. Cortona sits high enough that on a clear day you can see all the way to Lake Trasimeno, a hazy silver line on the horizon. The town itself moves at the pace of a nap: cats stretched across warm doorsteps, laundry lines strung between buildings older than most countries, an old man setting up the same three chairs outside his shop that he's probably set up every morning for decades.

I didn't do anything remarkable in Cortona. I mostly just walked, got slightly lost, and sat somewhere with a view longer than I meant to. Which, it turns out, is exactly the right way to visit.

Second Stop: Montepulciano, Where the Wine Outnumbers the People

By the time we reached Montepulciano, I'd already heard the rumor: that half the town is hollow. Not abandoned — just tunneled. Cellar after cellar dug beneath the main street, packed with barrels of Vino Nobile aging quietly while tourists walk overhead with gelato, completely unaware they're standing on top of a small underground city of wine.

We picked one cellar almost at random — the kind of decision that either goes wonderfully or forgettably — and it went wonderfully. A woman who'd clearly done this a thousand times poured us a taste of something dark and warm, and mentioned, almost as an aside, that Pienza's pecorino is not from Montepulciano, thank you very much, and the two towns have quietly disagreed about cheese and wine bragging rights for centuries.

I climbed the tower at Palazzo Comunale afterward, mostly to justify the second glass. The view from the top made it worth it regardless — rolling hills in every direction, the kind that make you understand why so many Renaissance painters never left this region for inspiration.

Last Stop: Pienza, the Town a Pope Designed on Purpose

Here's a fact that changes how you look at Pienza: none of it happened by accident. In the 1400s, a pope named Pius II decided to turn his hometown into his idea of architectural perfection — proportioned streets, harmonious piazzas, a whole town built like a diagram of the ideal Renaissance city. Walking through it feels almost too neat, like a stage set that people happen to actually live in.

And then there's the pecorino. Every third shopfront seemed to be selling wheels of it, aged in walnut leaves, coated in ash, buried in hay — each version tasting different enough that we ended up doing an accidental tasting tour without ever meaning to.

We ended the day at the belvedere behind the town, looking out over the Val d'Orcia as the light went gold. Someone nearby said the view looked fake, too perfect to be real. I didn't disagree.

Would I Do It Again?

In a heartbeat. Each town gave the day something different — Cortona the quiet, Montepulciano the wine, Pienza the light at the end of it all. None of it felt rushed, and none of it felt like "checking a box." It felt like an actual day well spent, which is rarer than it should be when you're traveling.

If you're weighing whether to squeeze these three towns into one day: do it. Just wear shoes that can handle a staircase or two.

Want to Skip the Logistics?

I'll admit the one thing I didn't love was figuring out parking in three different hill towns in one day. If you'd rather spend your energy on wine and views instead of navigating narrow medieval streets in a rental car, our private transfer service handles all of it — pick-up, drop-off, and a pace that's entirely up to you.

[Book Your Private Transfer →]

Curious about the rest of Tuscany? Read about Monteriggioni, Siena & San Gimignano · Pisa & Lucca · The Cinque Terre